Stepping Out: After the First Time (Part 2)

The first time I really had a good chance to really step out, I happened to have a week all to myself.  My wife was out of town you see, and that's a rare occasion.  Usually she's always here, and she would very much disapprove of me leaving the house in a dress. When she told me she was taking a trip, a plan began to come together in my head.

Yes, I know there are some of you who are probably getting an urge to type some sort of nasty message like, "How dare you do that to her.  You're a bad person."

Fine, I'm a bad person.  Can I get on with my story?

My initial preparations took place weeks before.  Ordering makeup was my first mission.  I knew that if I was going to do this right that I needed foundation, blush, eye shadow, mascara, eyeliner, and fingernail polish.  From my other experiences, I knew that I didn’t want to be seen as a man when I was out.

There was a lot to order.  I had no makeup, so I bought some large variety palettes for the eye shadow and blush, several colors of lipstick, lip gloss, and fingernail polish.  Also, I decided to order some other things like false eyelashes, fake nails, and a few other things.  I didn't want my week to come and not be prepared.

The items came, and I stashed them away so that I could initiate my plan.

The makeup sat there waiting for me all week, and then the day finally came.  When I got home from dropping my wife off at the airport, I was in heaven.  The world was my oyster for seven glorious days.  I started by epilating my legs, painting both sets of nails hot pink, and slipping into my best lingerie - an all silk tap panty and camisole set.  It was deliciously feminine, and I was enjoying it immensely, but I knew that wanted more.  My whole plan was to go out dressed as a woman, and that’s what I began to work on next.

Sitting in a chair with boxes of brand new makeup in front of me, I did my best with the makeup that I ordered online.  Unscrewing the top on the foundation, I began to apply it to my skin, and found out that yes, foundation should be purchased at an actual store.  It didn't look that bad though, and I began to apply the other makeup.  A girl would definitely find many critiques in what I did, but all I was interested in was passing while I was out.  As I looked at my reflection in the mirror, it looked to me like the makeup that I applied would do the trick.  All in all, it wasn't bad.  In fact, I think it was rather good, because that day, I don't think I was made by anyone, so I must have done a decent job of it.

It was still morning when I got ready to leave.  I had a whole day of being a woman ahead of me, and I knew that I wanted to go shopping.  That was my goal, to go panty and dress shopping in a big clothing store.  Slipping on a few outfits, I settled on my red dress with an accordion-pleated overlay and a black ribbon that tied at the waist.  It was pretty dressy for a Saturday afternoon shopping, but that's what I wanted to wear.  In my mind I told myself that I could be a girl who was on her way to somewhere formal, and just decided to do a little shopping.  That story sounded believable.

Up until this point when I went out dressed, I had hidden behind the safety of my big sunglasses.  Along with my wig they helped to hide my face.  Even if someone recognized me as a man, they wouldn’t know who I was.  Taking off those glasses was a big risk.  I had a big fear of running into someone that I knew at the store.  Going into the store would be a big risk too.  I had never done something this bold before.  I knew these things, but I willed myself to act. Pulling up to the store, I got out of my car.

"You're really doing this?  You're really going to go in there?  Are you crazy?" I said to myself as I felt myself in that dress in the naked sunlight, and saw myself emerge from the safety of my car.  Walking as gracefully as possible in my black heels, holding my shoulders back, and being loose, I remembered to feel feminine and smile.

I walked past a few people (In a dress!!!!) and they took little notice.  Then it was time...I walked into the entrance of the large clothing store.  The doors slid open, and I looked around at the bustling entrance.  People were coming in and going out and there were all kinds of people in line at the register.

This was the moment.  I took off my sunglasses and carefully put them in my purse.  I kind of waited for a reaction, but there was none.  There were no gasps, no one pointed; I didn't even get any looks.  I think people are just too busy and caught up in their world, for one thing, but I know if they would have spotted a guy in a dress, they would have at least given me that look.

The fact was, though, that they didn't.  No one looked, no one stared, no one did a double-take, no one laughed.  The register beeped, and people walked to and fro.  I was amazed.  I had passed on my first time going out dressed.  Casually and guardedly, I walked down the aisles of the store trying to enjoy my experience.

The fact that the store was so crowded obviously made me nervous.  People were walking by me every few seconds.  It was a lot more to mentally handle than I thought, especially when I was walking in that entrance.  There were so many people, it was intimidating to be in a dress to say the least, but the fact that I got no stares made me want to continue.

Carefully, I made my way over to the intimates aisle, and casually perused some of the panties.  It felt good to be able to touch and see them in person instead of online.  I could lift them, touch them, and it didn't seem weird to anyone because I was perceived as a girl, although I still felt like an imposter who shouldn’t be touching them.  I stayed there for about five minutes, and brimming with confidence wanted to do more, but I felt that this was enough for now.  I didn't want to press my luck.  Going back to my car, I got and pulled away, happy that I was safe, but a bit sad that I wasn’t shopping around people in my dress anymore.

On a high from my success, I drove home and saw another store that was having a big going-out-of-business sale. On impulse, I parked and went in.

It too was very crowded, and being in a dress around all those people was a rush, but still very scary.  Still, I felt a lot more confident since I wasn't getting any looks. 

I don't know particularly what I was afraid when I was at these stores.  In today’s day and age, I didn't have much of a fear of someone ripping off my wig and saying, "Look, he's really a boy!" but I did have a fear of maybe someone subtly pointing and snickering, and maybe drawing the attention of others.  The fact that none of this happened was awesome.

I went home confident that I had somewhat mastered this passing thing, however not all my experiences were as successful.  I would learn that in another outing.